Ethanethiol → HCID 19808776, compound

HRID 374042Notes

Reaction equation

HRID 374042 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(S)C.[CH3:8][N:9]([CH3:33])[CH2:10][CH2:11][N:12]1[C:20](=[O:21])[C:19]2[C:18]3[C:22]4[CH:28]=[C:27]([O:29]C)[CH:26]=[CH:25][C:23]=4[S:24][C:17]=3[C:16]([CH3:31])=[CH:15][C:14]=2[C:13]1=[O:32]>C(Cl)Cl>[CH3:33][N:9]([CH3:8])[CH2:10][CH2:11][N:12]1[C:20](=[O:21])[C:19]2[C:18]3[C:22]4[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:23]=4[S:24][C:17]=3[C:16]([CH3:31])=[CH:15][C:14]=2[C:13]1=[O:32]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 19808696HCID 19808696, compound

Product 1

HCID 19808776HCID 19808776, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

690 mg of anhydrous aluminum chloride was suspended in 100 ml of methylene chloride. To the suspension was added 1.1 ml of ethanethiol at room temperature, and the mixture was stirred at the same temperature for 30 minutes. Thereto was dropwise added, in 1 minute, a solution of 380 mg of 2-(2-dimethylaminoethyl)-9-methoxy-5-methyl-1H-[1]benzothieno[3,2-e]isoindole-1,3(2H)-dione dissolved in 100 ml of methylene chloride. The mixture was stirred at room temperature overnight. The solvent was removed by distillation under reduced pressure. The residue was mixed with 100 ml of ethyl acetate and 50 ml of an aqueous saturated sodium hydrogencarbonate solution. The mixture was stirred for 30 minutes. The resulting insoluble material was removed by filtration. The separated insoluble material was washed with 50 ml of ethyl acetate. The filtrate and the washings were combined. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from n-propanol to obtain 340 mg (yield: 93%) of 2-(2-dimethylaminoethyl)-9-hydroxy-5-methyl-1H-[1]benzothieno[3,2-e]isoindole-1,3(2H)-dione as yellow crystals.

Workup

  1. additionThereto was dropwise added, in 1 minute
  2. stirringThe mixture was stirred at room temperature overnight
  3. customThe solvent was removed by distillation under reduced pressure
  4. additionThe residue was mixed with 100 ml of ethyl acetate and 50 ml of an aqueous saturated sodium hydrogencarbonate solution
  5. stirringThe mixture was stirred for 30 minutes
  6. customThe resulting insoluble material was removed by filtration
  7. washThe separated insoluble material was washed with 50 ml of ethyl acetate
  8. customThe organic layer was separated
  9. washwashed with an aqueous saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customThe residue was recrystallized from n-propanol

Sources & evidence

ORD record
ord-ef54c1a6206f4da8924fc00a6cabba16
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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